14447-01-9Relevant articles and documents
Traceless Release of Alcohols Using Thiol-Sensitive Oxanorbornadiene Linkers
Aioub, Allison G.,Higginson, Cody J.,Finn
, p. 3233 - 3236 (2018)
A class of ester-amide oxanorbornadiene (EA-OND) molecules was developed to release alcohol cargos by succinimide formation upon addition of a thiol reagent. The resulting ring-closed adducts undergo further fragmentation by retro-Diels-Alder reaction to release a furan moiety in a manner similar to oxanorbornadiene diesters. The rates of each of these fragmentation pathways in the same medium were found to be sensitive to the steric nature of the amide substituent. Alcohol release was much faster in protic solvents than in aprotic ones, suggesting that this system may be useful for rapid response to thiols in biological environments. Accordingly, the attachment and thiol-dependent release of cholesterol was characterized as an example of the manipulation of a drug-like cargo.
Synthesis and characterization of a new two photon excitable acid sphingomyelinase FRET probe
Mohamed, Zain H.,Rhein, Cosima,Schmid, Benjamin,Tripal, Philipp,Kornhuber, Johannes,Arenz, Christoph
, (2021)
Recently, FRET probes for acid sphingomyelinase (ASM) have enabled the observation of enzyme activity in intact cells for the first time. Here we present an ASM FRET probe specifically optimized for 2-photon excitation. To facilitate probe characterization and comparison to the previous probe, we mixed the two intact probes with defined amounts of the probes' ceramide cleavage products and mounted them on lipid beads. Directly excited NBD FRET acceptor fluorescene proved to be a useful means of reference and showed that the new probe is brighter, albeit only moderately, than the previous one. The new probe was then used to detect inhibition by various ASM inhibitors microscopically for the first time. Also in cells, directly excited acceptor fluorescence proved to be a useful parameter in addition to FRET to visualize inhibition of ASM.
Synthesis and evaluation of D-thioluciferin, a bioluminescent 6'-thio analog of Dluciferin
Rylands, Marwaan,Jardine, Anwar
, p. 176 - 189 (2021/03/17)
All known light-emitting firefly-bioluminescent luciferin analogs are either derived from the 6'-hydroxy- and/or 6'-aminoluciferin. We report the synthesis of D-thioluciferin, a 6'-thio analog or isostere of D-luciferin, starting from p-aminothiophenol, using a unique thioacrylate-S-protecting-group strategy. Upon treatment of Dthioluciferin with purified Photinus pyralis (Ppy) luciferase (Luc), a bioluminescence emission with a red-shift λmax relative to D-luciferin was observed. It was also shown that disulphide and sulphide analogs of Dthioluciferin did not produce similar bioluminescences relative to D-thioluciferin when treated with Ppy Luc under standard conditions, thus, providing a foundation for the development of D-thioluciferin based probes based on disulphide reduction and S-dealkylation.
Solvent-free and montmorillonite K10-catalyzed domino reactions for the synthesis of pyrazoles with alkynylester as a dual synthon
Annes, Sesuraj Babiola,Ramesh, Subburethinam,Saritha, Rajendhiran,Shankar, Bhaskaran,Subramanian, Saravanan
supporting information, p. 2388 - 2393 (2020/05/13)
A highly regioselective, solvent-free and montmorillonite K10 clay-catalyzed domino process with an unprecedented ring-closing C-C bond-formation reaction is described for the synthesis of a new class of 1,3,4-trisubstituted and 1,4-disubstituted pyrazole
